82950-72-9

Basic information

• Product Name: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID
• Synonyms: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID;(S)-1-ACETYLINDOLINE-2-CARBOXYLIC ACID
• CAS NO: 82950-72-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Product Categories: pharmacetical
• Mol File: 82950-72-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 494.135°C at 760 mmHg
• Flash Point: 252.644°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID(82950-72-9)
• EPA Substance Registry System: (S)-1-ACETYL-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID(82950-72-9)

Safety Data

• Hazardous Substances Data: 82950-72-9(Hazardous Substances Data)

Usage

General Description

(S)-1-Acetyl-2,3-dihydro-1H-indole-2-carboxylic acid is a compound with a molecular formula of C12H13NO3. It is an indole derivative that is commonly used as an intermediate in the synthesis of various pharmaceuticals and natural products. This chemical has been investigated for its potential biological activities, including its antibacterial and antifungal properties. It has also been studied for its potential use in the treatment of cancer and other diseases. Additionally, (S)-1-Acetyl-2,3-dihydro-1H-indole-2-carboxylic acid may have applications in the development of new materials and as a building block for the synthesis of complex organic molecules.

InChI:InChI=1/C11H11NO3/c1-7(13)12-9-5-3-2-4-8(9)6-10(12)11(14)15/h2-5,10H,6H2,1H3,(H,14,15)/t10-/m0/s1

Upstream product

• 103476-80-8 1-acetyl-2,3-indoline-2-carboxylic acid 
• 108-24-7 acetic anhydride 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 82923-75-9 N-acetyl-(S)-2,3-dihydro-1H-indole-2-carboxylic acid 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 10441-26-6 N-acetyl-indole-2-carboxylic acid 
• 1477-50-5 Indole-2-carboxylic acid 
• 110659-07-9 N-acetyl-indoline-2-carboxylic acid methyl ester 

Downstream Products

• 110592-39-7 (S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester 
• 82923-75-9 N-acetyl-(S)-2,3-dihydro-1H-indole-2-carboxylic acid 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 82923-81-7 (S)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester 
• 79854-42-5 Ethyl (S)-indoline-2-carboxylate hydrochloride 
• 82923-76-0 (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride 
• 79815-20-6 (S)-indoline-2-carboxylic acid 

Relevant articles and documents

A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives

A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.

Asymmetric hydrogenation of 2-substituted N-protected-indoles catalyzed by rhodium complexes of BINOL-derived phosphoramidites

The rhodium-catalyzed asymmetric hydrogenation of 2-substituted N-protected-indoles using monodentate phosphoramidites as ligands was examined. Full conversion and 74% ee, were obtained with a catalyst based on PipPhos. The use of a catalytic amount of base is necessary for activity; best results were obtained with Cs2CO3.

NEW PROCESSES FOR THE PREPARATION OF OPTICALLY PURE INDOLINE-2-CARBOXYLIC ACID AND N-ACETYL-INDOLINE-2-CARBOXYLIC ACID

Processes for: a) separating the enantiomers of indoline-2-carboxylic acid of formula (I): comprising of: (i) combining the (R, S) indoline-2-carboxylic acid with (1S)- or (1R)-10- camphorsulfonic acid as the resolving agent in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-indoline-2-carboxylic acid with optically pure (1S)- or (1R)-10-camphorsulfonic acid; (ii) regenerating the (S)- or (R)-indoline-2-carboxylic acid from the crystallized diastereomeric salt by using a suitable base or basic ion-exchange resin; and b) for the optical resolution of N-acetyl-indoline-2-carboxylic acid of formula, (II): comprising of: (i) combining the (R, S)-N-acetyl-indoline-2-carboxylic acid with (S)- or (R)- phenylglycinol as the resolving agent in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-N-acetyl-indoline-2-carboxylic acid with optically pure phenylglycinol; (ii) regenerating the (S)- or (R)-N-acetyl-indoline-2-carboxylic acid from the crystallized salt by using a suitable acid or acidic ion-exchange resin. The non-selected enantiomer may then be racemized and the process (a) or (b) repeated thus to obtain substantial conversion of the material to one enantiomer.